Around My Heart In 21 Days
by DegrasssiLuva
Summary: When Jenny Humphrey returned for her brother's and Blair's wedding, she thought she could make it through the month without any problems. But seeing him again in his normal purple suit made everything very hard. Chuck Bass wanted Jenny Humphrey.
1. Chapter 1: Back and Bass

It had been 5 years, but to Jenny Humphrey it felt like just yesterday she had lost everything. Her friends, her family, and most importantly the guy she loved. And it was all because of one man. One man who took the only thing that was still special to her. But now that was gone. She could not believe that she was going back. Back to the place where she lost everything, but she wasn't going back for herself. She was going back for her best friends wedding. Even after everything, she was still asked to design the wedding dress for the wedding of **Blair Waldorf and Dan Humphrey. **Even Jenny herself couldn't believe that her brother was getting married to Blair Waldorf. Dan was from Brooklyn, somewhere Jenny thought Blair would never ever venture into. As she got down from the taxi, she looked up at the apartment in front of her. She could not believe she was back. The only people who knew she was back was her brother Dan, her father **Rufus**, Blair her future sister-in-law, and **Eric **her best friend. No one else knew, and she wanted it to be that way. But something stopped her from keeping it that way.

"Jenny?" a puzzled looking **Nate Archibald **said.

"Nate? What are you doing here?" she asked, shocked to see him.

"Serena lives here. She is my girlfriend," he explained. She knew this of course. She knew who was dating who, and what was happening. This was all thanks to Blair and Eric of course.

"Oh ya I heard," she answered.

"What are you doing back in Manhattan?" he asked.

"I am here for Blair and Dan's wedding. I mean he is my brother and all," I told him.

"Well it's great to see you back," he said. He hugged her. It was nice to feel his warmth. Jenny knew he was off limits. Especially since he is dating her step-sister. Jenny was starting a new, so nothing was going to ruin. "Do you need help with your bags?" She nodded. He grabbed one of her bags, and she took the other one and together they went upstairs. She was greeted by a suffocating hug from her father.

"Dad I missed you, but I would like to live to hug everyone else," she said, smiling. Despite this, she was so happy that he was happy that she was back. After pulling away from him, she saw Dan. She ran into his arms. She missed Dan the most, more than anyone else. Dan was the one she could always turn to. He hugged her tight, and she hugged him back as tight.

"Does the bride/ future sister-in-law not get a hug?" asked a petite brunette. Jenny smiled when she saw her.

"Of course you do, welcome to the family Blair. I am so happy you asked me to design your wedding dress." Jenny said, hugging her.

"And don't forget the bridesmaids dresses," Blair added.

"Who are they by the way?" Jenny asked curious.

"Serena is the maid of honour of course and she will be walking down the aisle with Nate. Then it will be you and some other people.

"Great, I will discuss them as soon as I get settled in."

"I hate to interrupt this moment, but does the step-sister not a get a hug." Jenny turned to see a tall blonde standing there smiling at her. Jenny went to her and hugged her.

"I missed you **Serena.** And of course I need your input in the bridesmaids dresses," said Jenny.

" The engagement party hasn't even started and I already have a headache," Dan complained. "Will you ladies stop discussing the wedding for at least 1 minutes so we can get Jenny settled in." Jenny looked around. She was so happy to be back. Dan, Rufus, Serena, Blair and Nate. They were all happy to see her, and this made it easier for her to fit back in. Now all she had to do was see Lily and Eric. And everything would be fine. There was only one person she didn't want to see, and no one had mentioned him … yet.

Once Jenny was fully settled Dan, Blair, Serena, Nate, Jenny went to Butter to meet Eric for dinner. When Eric saw Jenny, he almost killed her. This hug was worse than Rufus's.

"Eric…cant breathe…let go," Jenny said, trying to breathe. Eric pulled away.

"Sorry I just missed you so much. You don't know how long I have been waiting for you to come back." Jenny smiled, she knew Eric would always be there for her, through the thick and thin. Through everything, every time she messed up, he was always there. They sat down, Blair, Serena and Jenny immediately started discussing the dresses.

"So I looked over the designs you sent me Blair, and I have drawn a few sketches and you just have to put a tick next to your top 3. Then we can choose from those. I have brought my sketch book actually."

"Really you brought you sketch book," Dan said. Jenny gave him a look.

"I have less than 1 month to make 1 wedding dress and 3 bridesmaids dresses. So don't ask me questions," Jenny said. " But no rush Blair. I would prefer to have your answer by the end of the week though. I also have some bridesmaids designs. You and Serena can choose and tell me." She passed them the sketch book.

'Wow these look amazing," said Serena, looking amazed.

"Let me see," said Nate. He looked at them, and also opened his eyes wide. "These are brilliant."

"I know which 4 I have chosen as the top ones for bridesmaids," Blair said.

"Which ones?" Jenny asked.

"Definitely 9,8,4, and 1." Blair said. Serena nodded in agreement. 9 and 8 were Jenny's favorites too because they were inspired by the truth. They spent the rest of the meal discussing how Dan proposed. It was good first meal back in New York for Jenny. She felt comfortable with these people. She finally felt back at home. But what she didn't know is that this feeling wasn't going to last for long.

-"Why can't I come to this?" asked Dan. It had been a week since she had been back. There were 3 weeks till the wedding.

"Because this is a girl's only brunch, and anyway you have other work to do. Like planning the wedding," said Serena, Nate and Dan had been grounded at the loft. Blair, Jenny and Serena were going to go out for brunch, then go to the spa. On the way to brunch, Jenny saw a familiar limo pull up in front of the restaurant.

"Oh no." she whispered. Blair and Serena looked at the limo, they froze. This couldn't be happening the all thought, everything was going so great. They immediately turned to Jenny, she was frozen. She wasn't ready. She had been back for a week, and everything was going amazingly well. She had already started on the bridesmaids dresses, she had finished two of them. Once she finished the last one, she would be starting on the wedding dress.

"Jenny I swear, I did not know that he was going to be here," Blair said. She was very worried for her future sister-in-law. Jenny felt a tear develop in her eyes. She saw the familiar figure step out of the limo. She thought she was ready, she knew that she couldn't hide from him forever. But she was hoping forever would last a little bit longer. She knew right then and there, that she wasn't ready for this. She thought she was but she wasn't.

"Blair, Serena. Could I please speak to Jenny in private?" he asked.

"**Chuck** I don't think that is a good idea," Serena said.

"I am not going to do anything, I just want to talk to her. Nothing more, nothing else," he said, he looked straight into Jenny's eyes. But she looked away, she was not going to fall again.

"I'm sorry but we have important wedding details to discuss," Blair told Chuck. But he wouldn't leave.

"Just 30 seconds is all I need," he said, he sounded like he was going to start begging. So Jenny gave in, she nodded.

"Jenny are you sure," Serena asked.

"It's just for 30 seconds, what's the worst that could happen," she said. But she knew what could happen. Serena and Blair walked into the restaurant. Chuck reached out for Jenny, but she pulled away.

"You have 25 seconds remaining, say what you need to say. I don't have all day," she said, coldly.

"I'm sorry. I know you won't believe it, but I am. I didn't think you would leave for 5 whole years. I also didn't know it was your first time. I thought you did it with Damien. I didn't want you to be so mad at yourself, or me. But Jenny, running away isn't the solution Jenny. Tell me you didn't feel anything that night and I will leave you alone," he said, this time when he looked into her eyes, she didn't look away. She couldn't, but she was not going to fall this easily. She looked away and spoke 5 words that she didn't think would affect Chuck at all.

"_I hate you Chuck Bass," _she said, and after she saw his face fall. She walked away fast.

"_I will get you back Jenny Humphrey _I don't care what you say," he whispered, so that only they could her. She rolled her eyes. She knew this was going to be a long 3 weeks. But she didn't think it would be this eventful.


	2. Chapter 2: Flowers and Fun

Jenny was in her room when she heard a knock on the door.

"Come in," she called. She saw Lily come in with a bunch of roses. There were the prettiest roses that she had ever seen.

"Aren't they gorgeous? They came for you with a note," Lily said. She showed the note to Jenny.

_Roses are Red_

_The Sky is Blue_

_There is only one girl I want to be with_

_And that girl is you_

_Xoxo_

Jenny stared. As pretty as the roses were, if Chuck wanted her back he had to do much more. She smiled as the read the note though. She was going to get Chuck to beg, even if it hurt her in the process. She knew that he would do anything to win. But something was very different about this time. What he wanted to win… was her heart. So he really needed to step up his game.

Chuck was reading some files when Nate came in with flowers.

"Really Nathaniel I thought you were more romantic that flowers. But I'm sure anything is good for Serena," Chuck said as he saw the flowers.

"They aren't for Serena, they're for you," Nate said.

"Umm as much as I love you Nathaniel. That love is brotherly love," replied Chuck. Nate laughed.

"They are from someone else, there is a fine line when it comes to bromance. And I don't plan on crossing it." Nate said, he passed them to Chuck. Chuck laughed as he read the note.

_As sweet as you that was_

_You are going have to try way harder_

_But remember my heart is locked away_

_So keep trying and one day it might just work_

_Hugs and kisses_

_-J_

He was ready for the challenge.

"Nathaniel, I have a serious question for you and you are not allowed to ask questions or laugh or anything," Chuck said to Nate. Nate got a little worried.

"Ask me anything," Nate said. He was scared of the question.

"How did you get Jenny to fall for you?" asked Chuck. Nate froze, did he just ask the question Nate thought he asked.

"Wait Jenny as in Jenny Humphrey," asked Nate. Chuck nodded as he rolled his eyes. "I don't know Chuck. I guess I was always there for her when others weren't. Also I don't sleep around with a lot of girls." That last part caused Chuck to hit Nate on his back.

'Thanks for that Nathaniel and as for that last part. It is not funny anymore," and with that Chuck left. Nate stared at his best friend in shock. Since when did Chuck Bass care about a girl, except for Blair of course. But he was over her. I mean he asked Nate how to make Jenny fall in love with him. Nate immediately took out his phone and called the only person he could think of calling.

Lunch with Blair, Jenny and Eric was fun for Dan. When he phone rung he hardly wanted to pick up. But he did anyway.

"Hello"

"_Dan, Chuck is in love with Jenny." _Dan spat his water out, all over Eric.

"What the hell? Are you serious? Sorry Eric."

"_Yes he just asked why Jenny fell in love with me. Don't tell her I said that. But this time I think he actually does like her"_

"Are you sure? I don't want her to get hurt again."

"_He has never asked me for advice before, so I am pretty sure it is serious."_

"Ok thanks for the heads up, and I better hang up and explain to Eric why I spat water all over him." He could hear Nate laugh. Dan hung up and shot Eric an apologetic look.

"You better have a good reason for your spit being all over me?" said Eric, wiping himself.

"I do. Jenny is there something you have to tell me?" he shot Jenny a "I know what you're hiding" look. But she was just confused.

"No, not that I know of."

"So you weren't going to tell me that Chuck is trying to win you over." Jenny suddenly froze.

"Nate called you didn't he." Dan nodded. Blair and Eric just watched as the siblings discussed the Bassman.

"Don't worry Dan, I am playing hard to get. He wont get me unless he does something really nice for me."

"Jenny, I don't want you to get caught in one of his Bass games."

"Don't worry, I have everything under control. He isn't going to win so easily. Flowers aren't going to do the trick." After that the lunch continued, but it was way more awkward that before.

Chuck had ordered chocolates to be delivered to the Van der Woodsen apartment. But he wasn't done with that. He was planning something extravagant, he just needed some time to do it.

When Jenny got the chocolates, she was happy. She knew this was going to be fun. But she didn't think she would be having this much fun with this. She read the new note.

_Here are some chocolates for my sweet_

_They are here for you to eat_

_Whether you like it or not_

_This is a battle that will be well fought_

_-C_

She couldn't help but get butterflies in her stomach. She was actually having fun with this. She hated to admit it, but this was the most fun she'd had in 5 years. She then decided what she wanted to do the rest of the day. She got a taxi and went to the Empire. When she knocked on the door, a surprised Nate opened it.

"Jenny what are you doing here?" he said. She stepped in, and saw a handsome Chuck Bass sitting on that sofa.

"Chuck, " she said. He saw her and stood up immediately.

"Umm I'm just going to leave," Nate said, he grabbed his jacket and left. Jenny walked up to Chuck, but stopped literally 5 inches away from his face.

"I want you to show me the time of my life Chuck. Today, right now. Anywhere in the world, I want to have the best time of my life before I leave and go back. And I want al the people I love to be with me." He saw the hope in her eyes, and couldn't say no.

"I'll get my jet ready. Meet me at JFK in an hour and then we can go anywhere you want to." And with that she left, and he got everything ready.

When everyone was at JFK, they were glancing around. No one knew why they were there, but they knew it was important.

"Ok I know this is drastic, but I want each and everyone of you to think about it before saying no. I am leaving after the wedding and I just want to have the best time of my life before I have to go back. And I want all the people I love the most in this world to be with me when I am having the best time in my life." Jenny looked around at the faces, then at Chuck. He nodded and she continued. " We have Chuck's private jet to take us anywhere we want, in 3 weeks. And we will be back 2 days before the wedding. Imagine it, we can go any where we like. Each of us can pick a location and we will go there for 3 days and then we will go to the next place. Even though it is not for long, you can always say in the future. I have completed my dream of going to wherever you want to go,"

"I'm in," Chuck said.

"So are we," said Nate and Serena. Eric nodded and took Jenny's hand. It was now just Vanessa, Dan, Blair, Rufus and Lily.

"I'm up for it." Vanessa hugged Jenny.  
"I don't know.." Rufus began to say.

"I say we go." Blair said, this shocked everyone. Everybody expected her to be the one who objected.

"I have only 3 weeks till the best day in my life. And I want to spend as much time as possible with all the people I love." Dan took her hand and nodded.

"I guess it wouldn't be that bad." Rufus said, and Lily nodded.

"YAY!" Jenny said clapping. "Now don't worry about clothes or anything everything has been done for you. Now once we are on the plane we will decide where we are going to go." They all did a huge group hug and went onto th private jet. Nate and Serena were sitting next to each other. Vanessa would be next to Jenny. Eric was next to Chuck. Dan and Blair were next to each other and so were Rufus and Lily. Jenny and Chuck stood up.

"So who's first." Everyone looked at Vanessa. She rolled her eyes, but she thought hard. Jenny saw her eyes light up. Vanessa whispered in Jenny's ear

"Ok so the first place we are going to is Haiti. That is Vanessa's choice and since she is getting off there to go live there. We will spend 2 days there and then the next place will be Eric's choice. Also remember you are not allowed to tell anyone where your choice of place is till it is your turn." When the finally reach Haiti, Vanessa bid them goodbye at the airport. When the got to the hotel, the rooms were as following. Nate, Dan, and Chuck were sharing one suite. Blair and Serena were sharing another suite. Eric and Jenny would share another suite, and Lily and Rufus would be sharing a suite.

"Ok if we are definitely doing this I have only one rule." Rufus stated before he and Lily went into their room. " That rule is what ever that is said or done on this trip stays with the trip. Unless it is something life changing. When it's the wedding I want everything to be perfect for Dan and Blair." Everyone nodded in agreement. Jenny and Eric got changed and immediately went to hang out by the pool. Jenny was wearing a yellow bikini with a yellow sundress on top. Eric was wearing trunks and a t-shirt. Jenny was tanning herself, when a shadow appeared over her. She opened her eyes to find Nate looking down at her.

"Nathaniel, why are you blocking my sun?" she asked, sitting up.

"I need you help." "

With what?"

"I want to propose to Serena, and I don't know where she will pick"

"Why are you asking me? Shouldn't you be asking Blair."

"I would but I don't want to stress her out with this."

"Well if I know Serena, it's that she would like it to be simple and the real you. Don't go too crazy, but don't go too simple."

"Thanks Jenny." She smiled, as he walked away. It felt good to help a friend in need, even if she did used to love that friend. She looked around and saw Chuck at the bar. She went over to him.

"It's time to start the games." He looked at her. "You now officially have 3 weeks to win my heart." He nodded and stood up. Then he kissed her cheek and walked, she could feel her self blush. She knew then and there, that she had feelings for Charles Bass. But she just didn't want to show it…yet.


End file.
